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Synthesis in the Key of Catellani: Norbornene-Mediated ortho C–H Functionalization

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C-H Activation

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 292))

Abstract

In the late 1990s Catellani reported a remarkable palladium-catalyzed domino reaction [1] in the presence of norbornene, in which aryl iodides were alkylated at the ortho positions by alkyl halides followed by a Mizoroki-Heck reaction to afford products of type 1 (Scheme 1) [2–4]. The process allowed for the construction of up to three carbon–carbon bonds in a single reaction using simple, commercially available starting materials. We called this process the Catellani reaction, and in the past decade considerable attention has been focused upon unlocking its synthetic potential. This review will primarily focus upon the mechanistic aspects of the Catellani reaction, followed by an overview of the synthetic scope of molecules currently accessible with this technology.

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Authors and Affiliations

  1. Department of Chemistry, University of Toronto, Toronto, ON, Canada

    Andrew Martins, Brian Mariampillai & Mark Lautens

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  1. Andrew Martins
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  2. Brian Mariampillai
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  3. Mark Lautens
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Correspondence to Mark Lautens .

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Editors and Affiliations

  1. Scripps Research Institute, N.Torrey Pines Rd. 10550, La Jolla, 92037, USA

    Jin-Quan Yu

  2. College of Chemistry, Peking University, Chengfu Road 202, Beijing, 100871, China, People's Republic

    Zhangjie Shi

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Martins, A., Mariampillai, B., Lautens, M. (2009). Synthesis in the Key of Catellani: Norbornene-Mediated ortho C–H Functionalization. In: Yu, JQ., Shi, Z. (eds) C-H Activation. Topics in Current Chemistry, vol 292. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2009_13

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